


Sexual Connoisseur

by Ms_Tassimo



Category: Supernatural
Genre: Alternate Universe - High School, Bad Boy Castiel, Bottom Dean, Fluff, Loss of Virginity, M/M, Nipple Play, Top Castiel, Virgin Dean, ebay, i guess
Language: English
Status: Completed
Published: 2016-03-17
Updated: 2016-03-17
Packaged: 2018-05-27 07:02:00
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,706
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6274477
Author URL: https://archiveofourown.org/users/Ms_Tassimo/pseuds/Ms_Tassimo
Summary: <blockquote class="userstuff">
              <p>It's totally normal to order condoms off of eBay, right?</p>
            </blockquote>





	Sexual Connoisseur

Dean isn’t sure what compelled him to think that this was a good idea. There were a dozen different ways he could have done this without resorting to eBay. In fact, the more he thinks about it, the more absurd it begins to feel. If only he hadn’t let embarrassment consume him; the thought of waltzing into the pharmacy, picking up a box and then wandering over to the counter to pay Mrs McAllister makes him blush. She’d known Dean since he was five. There was no way she wouldn’t mention it to his dad or Bobby, and then he’d have to have the awkward conversation that he so wasn’t ready to have with anyone.

Neither did he want to approach the superstore on the outskirts of town, where a large number of his classmates worked in the evenings and weekends. Because if he went there and they saw what he was purchasing, he knew that he would be the talk of school by the Monday. No, this was why Dean had seen internet shopping as a better method. 

But there was also a reason why Sam was the one to do computer work. 

Give Dean a car, and he can fix it. Give Dean a cigarette, and he can smoke it. Give Dean a computer? Prepare yourself for the slowest transaction you’ve ever witnessed. It had taken twenty minutes for him to find what he was looking for, and another ten to work out how to work out how the damn site worked.

However, finally, Dean was clicking the small BUY NOW icon, holding his breath as he did so. He knew that he’d need to work out how to wipe the history, but he’d deal with that once he’d paid for the delivery and stuff.

He tried not to think about the sort of people who sold condoms over the internet.

***

Dean almost literally spends the next week sitting by the postbox; the last thing he needs is for Sam or his dad to open his mail accidentally. It’s all becoming a bit out of proportion, really; he’s seventeen, it’s not like he’s the only kid about to have sex for the first time, right? There were guys who came into class after the weekend, bragging about how many girls they’d nailed on Saturday night. Surely they must have to buy condoms too, right? Or maybe they let the girls do it? Maybe there was a secret place girls went to-

Whatever. All Dean knew was that he was more scared of getting the condoms than losing his virginity. He’d worry about that after the first hurdle was out of the way.

It’s a Friday that they arrive; neatly wrapped in an inconspicuous brown box, which he opens in the privacy of his own bedroom, he holds the box of condoms in his hands. The words on the front are in Chinese, which doesn’t really help Dean much, but surely they all do the same thing? Kind of a one purpose sort of thing?

Soon, Dean’s fingers are trembling as he sends a text. He pulls his boots on and shuts the door quietly, even though Sam’s at the library and his dad is out God knows where. Was it meant to feel like he was walking to the gallows? Dean had spent so long overthinking this and worrying about the condoms, that the actual sex didn’t actually seem like a huge issue.

But he knows that as soon as he arrives at the house, it’ll hit him. It isn’t like he shouts from the rooftops that he, Dean Winchester, is a virgin. Sure, he’d fooled around with a couple of girls before, he wasn’t that inexperienced. But given that it was only in the last year that he had come to the realisation that he liked guys, sex hasn’t been high on his list of priorities. But now it is. And it’s here. 

Dean clears his throat and knocks the door with his knuckles in quick procession, looking around the street, the box burning in his pocket. He regards the neighbours in their front lawns, on this lovely summers day; what if they know what he’s about to do? What if they’re trained to look for suspicious packages-

The door swings open, and Dean stares for a moment, his eyes wide.

Castiel Novak’s body is no stranger to him. On the contrary, their relationship had allowed Dean to touch almost every bit of his body without any protest. But at the moment, Cas is miles away from the composed, smartly dressed boy in the grade above Dean. He’s currently sporting some serious bed hair, black tufts sticking up in every direction imaginable. Dean’s gaze travels down from his face, trying not to catch the electric blue eyes that are trained on him. 

His torso is exposed, toned and lean, an out-of-character tattoo of scrawled writing on his hip. The same hips that jut out and frame the temptatious V shape that disappears into the waistband of grey sweatpants he’s wearing. 

“Wondered if I was going to see you again, Winchester,” Castiel remarks, pulling the door open for Dean. 

Dean walks in slowly, trying to give off the breezy air that he has at school. 

Some teachers would label him as arrogant, a miscreant and/or a pain in the ass. And sure, sometimes when Dean plays up, it’s just to get out of class for a few periods because he can’t stand the lesson. But – and he would never admit this to anyone, no way, no how – it all seemed to be a front. Because as much as teachers wanted to make excuses for him because his “mother died in a traumatic accident”, Dean liked the fact that other students gave him a wide berth. 

He didn’t need people to pander to him or latch onto him; it was pointless. 

And Cas-

Well, Cas was the exception.

Dean walked over to the coat stand, shrugging off the leather jacket that he was Goddamn melting under. He could feel Cas’ eyes boring into the back of his head, no doubt waiting for a reply that Dean wasn’t sure his mouth could manage. He casually tosses the box of condoms at Cas without meeting his eyes as he turns, his jaw clenched and his eyes focused on the carpeted floor.

Castiel chuckles, closing the space between them and slipping a long finger under Dean’s chin. He tilts it upwards, so that they’re looking each other in the eye. Dean can see the spark dancing in Cas’ eyes, pupils dilated. Dean can see every little mark on the other boy’s face, his long eyelashes beating together softly as Castiel slowly blinks.

“What’s up, Winchester? You scared?”

Dean swallows, feeling completely and utterly naked, despite having more clothes on than he has done all summer. He’s not…scared, as such. 

No. Fuck that. He’s scared.

“Like hell I am.”

Castiel nods absently, moving the finger that’s supporting Dean’s chin and running it along Dean’s cheek lightly. Dean’s breathing comes in light huffs, ashamed of the fact that Castiel’s starting to crack his façade. 

“You sure you want this, Dean?” Castiel murmurs, dipping his head and brushing his lips against Dean’s. His soft breath tickles Dean’s skin, sending the hairs on the back of his neck upwards. In response, Dean presses forwards, kissing Castiel sweetly in a fashion that was almost foreign to the two of them. So long they had spent their relationship having rough, heated moments as quickly as possible, that they, for one reason or another, hadn’t ever had time on their hand. 

Dean is determined to make the most of it while they have it.

Castiel gently presses Dean against the wall, his thigh slipping between Dean’s legs. Dean lets out a small gasp as he nips Castiel’s lower lip, taking advantage as he flicks his tongue into the wet heat of Castie’s mouth, trembling hands threading through Castiel’s dark hair.

The only thing that stops Dean’s jelly legs is Castiel’s thigh, and as the kiss deepens, they become more and more frantic, more familiar now. Dean ruts against Cas’s leg, cock straining painfully against the confines of his jeans, every judder of his hips causing him to whine in desperation. He finds it embarrassing how fast it’s taken him to go nought to hard so quickly, but he can’t dwell on it just now. Instead, he thrusts his hips desperately, feeling the grind of Cas’ dick fighting back against him.

Cas attacks him in a kiss, one hand wrapping around Dean’s wrists and pushing them above his head, causing Dean to moan loudly. The other hand slips downwards, skilfully undoing Dean’s belt with ease and teasing the button of his jeans. 

“Fucking tease,” Dean manages to gasp out against Cas’ lips. Cas grins wolfishly, dipping his head to nip the pressure point in Dean’s neck, before flicking the pain away with his tongue. 

The front of Dean’s briefs are damp with pre-cum and, shit, he’s not going to be able to last much longer at this rate. Almost as though he’s reading Dean’s mind, Castiel shakes his head, moving away quickly and sending Dean stumbling across the hall. He just about manages to avoid smacking his cock off the opposite wall, crying out in need.

“Not here, baby,” Castiel murmurs, taking Dean by the wrist.

How the hell Dean manages to get up the stairs is, and will remain, a complete mystery. But he finds himself on his back, still clothed, whilst Castiel hovers above him. Dean pants, his back arching as his dick throbs, desperate to come.

But Cas still takes his time; he presses his lips to Dean’s, biting his lip once more and sliding his hands under the shirt he’s wearing. Dean presses into his hands, his eyes scrunched closed and sweating under the clothing he’s so desperate to shed. And when Dean feels Cas’ fingers tweaking his fucking nipples, he wonders if sex is just another word for torture.

Cas ducks, his lips landing on Dean’s abdomen, grinning up at the boy underneath him. Dean can hardly see past the fuzz in his brain and concentrate on something other than the desire to come, but he feels Castiel’s lips moving over his skin, his hands pushing his shirt up as he does so. Dean’s skin fizzles, a buzzing sensation filling his entire body. Castiel’s tongue flicks Dean’s naval, and he bucks his hips, trying to find some part of Castiel’s body to grind against and help put an end to the raging hard-on that Castiel seems to be punishing him with. When Dean’s shirt is all the way up to his neck, Castiel’s teeth clamp down lightly around his nipple, his tongue flicking the sensitive nub gently.

“Holy fuck,” Dean manages to gasp out. “C-Cas, just hurry the fuck up.”

“Now, now, Dean,” Castiel replies in amusement, removing his mouth from Dean’s chest and tugging his shirt over his head. “Foreplay is one of the better parts of sex; I thought you would have known this being the sexual connoisseur that you are.” 

Dean can’t say anything; he wants to sob now because he can’t fucking come, and there are sensations that Castiel is making him feel that send rockets shooting into his brain.

Slowly, slower than it needs to be, Castiel undresses him. He starts with the shirt, making sure to lavish every part of Dean’s skin with a kiss, before making his way back down to the waistband of his jeans, hot breath making Dean’s treasure trail quiver.

“How much would you like my mouth on your cock, Winchester?” Castiel asks casually, gently pulling the offending garment down his legs. “Because from the looks of it,” they both stare at the way Dean’s dick shoots up now that it’s freed from its denim prison, “you’d love it.

“But,” Castiel continues, pulling Dean’s boots from his feet and throwing them over his shoulder, “that’s not why we’re all here today, is it?” Dean has never felt more aroused as Cas’ words wrap themselves silkily around his brain, holding him tightly. When Cas has discarded the soaked pair of briefs Dean had been wearing, he sits up, already tugging his own clothes off. 

“I want you to sit up on your knees, Winchester,” Cas demands, “face the wall.” Dean frowns, feeling the mood dropping. Hell, if he’d known that sex with Castiel would involve so much bossing about, then he’d have said no. But he does what he’s told, the air around him making his entrance twitch, despite the heat in the room.

He hears rather than sees Castiel reaches over for something in the bedside table, and Dean hears a morose squelching sound as Cas squeezes lube onto his fingers. Dean braces himself for the intrusion, the painful burn that he’s read about on his limited access to the computer. He feels Castiel’s finger push into him, and squeezes his eyes shut, trying not to make a single noise.

When Cas starts to move, Dean’s mouth opens slightly, and he finds himself rocking on the digit, practically squeaking when Cas adds another finger. Dean wets his lips, his skin covered in a thin film of sweat, hips rocking hopefully against Cas’ hand. Castiel’s other fingers are busy tweaking at Dean’s nipples again, the push of his fingers and pull of his fingertips simultaneous.

“You ready?” Dean barely hears Castiel say, too wrapped up in the haze of his mind to really register the tear of a packet and the squelch of more lube. But what he does feel and register is something much larger and thicker than fingers at his entrance. Dean exhale, panting as he presses his back against Cas’ clammy chest, a hand wrapping around the base of his dick without warning.

As Castiel pushes into Dean’s ass slowly, he also drags his hand up the length of Dean’s cock, distracting the younger boy from the initial burn of being penetrated.

God, Dean feels so fucking full. He lets out a moan, head tilted back as Castiel captures his lips with his own, swallowing Dean’s whimpers as he thrusts slowly. Dean exhales deeply, moving his hips to match Castiel’s careful pace. The hand on Dean’s dick moves painfully slow as well, and Dean finds himself bucking in frustration.

“Impatient, Winchester?” Castiel asks lightly. How the fuck is he still coherent?

“J-Just hurry the fuck up, asshat.”

And then Castiel stops. 

He fucking stops.

“Sure?” Castiel’s lips are nibbling the side of Dean’s neck now, still deep inside him and acting as though he’s commenting on the weather.

“Just do it already!”

And like that, Castiel starts to snap his hips, removing the hand from the base of Dean’s dick and holding him in place. Dean lets out a guttural moan, rocking back against Castiel as though his body depends on it. He can feel every little jolt and movement and it feels like his blood is boiling him alive from the inside out, as Castiel slips in and out of him, hands roaming everywhere as the pair blindly feel.

“I love how I’m the one who sees you like this,” Castiel all but growls, thrusting his dick and successfully hitting Dean’s prostate. “How you make all those little noises just for me.” He’s panting now, sweat glistening on his forehead as he snaps his hips, Dean’s head tilted back as he moans wantonly. His cock is swollen to the point of pain, teetering on the verge of coming but not quite able to get there. 

His cheeks are flushed pink, and his thighs burn from sitting up on them, and his nipples ache from being played with, and his stomach is taut with imminent orgasm. Cas’ fingers barely have to slip around his girth, giving a few half-hearted flicks of his wrists before Dean cries out loudly, cum shooting across his stomach as a torturous twenty minutes worth of erection spends itself.

Cas gives a few more thrusts, his hands gripping Dean’s hips so hard that they’ll probably leave marks and orgasms himself, groaning just as loud as Dean had and burying his face in his hair. The pair pant, their bodies one. There are butterflies in the base of Dean’s stomach as he reaches around and puts his fingers through Castiel’s hair, trying to catch his breath. 

Saying nothing, Castiel slips out of Dean with a wet “pop”, easing away from him to discard of the used condom. He casually tosses it into the waste paper bin, flashing the flushed expression on his face to Dean, who falls forward carefully, trying not to land on his still-sensitive dick, buries his face in the soft pillows of Castiel’s bed, breathing in the scent. Moments later, he feels the mattress dip, and Castiel lies next to him, his elbow propped up on the pillow next to Dean’s, his hand resting on the small of Dean’s back.

Cas’ fingers on Dean’s back feel heavenly, the tips caressing the skin as though following a secret map. He smiles into the pillow, not quite ready to shatter the calm. He can just see Cas from the corner of his eyes, the older boy stretched out against Dean, his heat enveloping him. Dean can let his eyes roam the twitching muscles in his boyfriend’s arms without interruption, and drink in the sight of his taut physique as he moves his fingers up and down Dean’s back.

Dean can now tell people about the scars on the backs of Castiel’s left thigh, or about the birthmark hiding beneath his briefs. He can tell people about the small, almost unnoticeable dent on Cas’ knee from falling on class whilst playing with his brothers.

Tiny things, a matter of moments, all privy to Dean’s knowledge. Hidden, a secret he’ll never share.

“You okay?” Cas murmurs, pressing his lips to Dean’s hair gently. Dean smiles again as Cas pulls their bodies flush, the latter’s erection starting to stir once more. 

Dean hums in contentment, turning his head to look at Castiel.

“Yeah,” he mumbles, kissing Castiel’s nose lightly. He grins, lips pulling back and showing Dean pearly white teeth. The guy was perfect. There’s silence for a moment, both boys just taking each other in. At this moment in time, Dean feels like they’re the only people in the world. Outside of this room, there is merely white noise.

“Wait,” Dean says suddenly, clocking the unopened box of condoms next to the door and breaking the silence. “Did…you get a condom out of your bedside cabinet?” He wrenches the drawer next to the bed open, staring down at the numerous condoms and bottles of lube. The owner of which was now sitting up slowly, rumbled.

Those same white teeth slip into Cas’ lower lip, a sheepish grin playing around his features. But Castiel isn’t blushing, oh no. This is the face of a guy who has been rumbled, whose little game has been exposed.

“I wanted to know that you were sure about this,” he says in reply, gesturing at their entwined bodies. “Wanted to know that I wasn’t pressuring you into losing your virginity- Yes, Dean, I knew you were a virgin,” he says with a wave of his hand as Dean opens his mouth to protest. “If you bought the condoms, then great. If not, then I was prepared to wait.”

This takes a moment for Dean to register. It was sweet in a kinda devious way, he supposed. And at least he knew now that Castiel definitely wasn’t with him just for the sex. Yep, Dean can live with the deceit. And just as he’s about to settle back down into the arms of Castiel Novak, the asshole opens his mouth.

“You do realise those condoms were out of date though, right?”

Dean’s eyes fly open, rolling out of the bed as he clutches the sheet around his hips, pretty sure he’s just flashed Castiel’s neighbour.

“What the hell do you mean they were out of date?!” Castiel hums as he reaches over the side of the bed, picking up the discarded box of condoms and pointing to a small bunch of numbers on the bottom of the box. Dean squints but he genuinely can’t see where the out of date sticker is.

“Yeah, they’re like a year out,” Castiel says like it’s no big deal. “They’re kinda strange though anyway; where did you get Chinese ones?”

Dean can feel the tips of his ears starting to burn. He can feel all of the bliss that he had felt not three minutes ago ebbing away in despair. 

“…eBay. I got them off eBay.”

A beat drops.

“You bought condoms off eBay?” Cas asks incredulously. “Damn Dean, why?” Dean feels his cheeks burn in embarrassment, mumbling about not wanting to be seen buying them in town. When he looks up, Cas is pressing his lips together in suppressed mirth, his bare shoulders shaking with the effort not to laugh.

“How was I supposed to know they were out of date?” Dean demanded, the flush spreading to the tops of his ears. “They were, like, a bulk buy thing!” Castiel shakes his head, smiling faintly. He puts his hand out for Dean’s, and the younger boy grudgingly takes it, allowing himself to be pulled back onto the bed. There, Castiel manoeuvres him so that they’re lying entangled, Dean’s head rested on Castiel’s chest as the latter runs his fingers through Dean’s short hair.

“You’re so cute.”

“I am not fucking cute, Novak.”

Cas snorts and says nothing, the pair of them lapsing into silence. Dean closes his eyes, revelling in the comfortable warmth that radiates from Castiel. Okay, so buying condoms from eBay hadn’t been his finest idea but, hey, there they were, closer than he thought two people could be. He feels sated and insanely at ease, something that he’s struggled with since beginning their relationship. 

Dean lets the smile spread across his features, pressing close to Cas. 

“I’m flattered though,” Castiel says, and Dean can feel him stretch to pick up the box. “Extra large, Dean?”

“Just shut the fuck up.”


End file.
